The Ultimate 12-day Itinerary to the Hawaiian Islands
The Hawaiian Islands offer much to do, see and eat— all while you’re surrounded with the most majestic scenery. Here is how we went to all 4 main islands in 12 days— during May 2021. I say this to give you an idea of the Covid Restrictions in place.
Overall the main key is to plan early, and make reservations well in advance as a lot of people plan Hawaii vacations a year in advance which makes last minute reservations for rental cars, hotels, restaurants and excursions hard to come by.
Here is our journey from Oahu, Kauai, Maui and Island of Hawaii.
OAHU
Day 1— fly into Oahu. We took a 10 hour flight from Charlotte, North Carolina and were pretty tired when we arrived around 4pm, but we were so excited to be there.
We went during the Covid Restrictions and once we got off the plane we were ushered into a line to check our Travel Hawaii account. Even now, you will need to make an account with Travel.Hawaii.gov— you can click here for their website. Here you will find an up to date resource of all the requirements to enter Hawaii now.
Our experience required a Negative PCR Covid test from a Trusted Testing and Travel partner. Walgreens and CVS are included in this and offer FREE testing. We tested with Walgreens and CVS throughout our time in Hawaii and were able to receive results within 72 hours for all 4 of our tests. Your negative covid test MUST be back before your flight leaves the mainland for Hawaii.
You can make an appointment with Walgreens here. Make sure to do so at least 3 days prior to when you want to schedule the test to ensure appointment availability.
You can make an appointment with CVS here. Make sure to do so at least 3 days prior to when you want to schedule the test to ensure appointment availability.
Once you arrive, they will ask for your QR code— you will receive this via email once you complete the Travel Hawaii portal, you will also present your license or another form of ID. They verify all your documents and you are good to go. This is not something you can bypass— even if you somehow slip past them, you will have to show your Travel Hawaii account to check into a hotel, rent a car, go on excursions and to eat in some restaurants.
We took an Uber from the airport— there are plenty available and reasonably priced, to our hotel. We stayed at Ala Moana Honolulu by Mantra located just outside of the true Waikiki area. It was about a 5 minute drive to downtown Waikiki which is where most everything is located.
We grabbed dinner at Hideout at Laylow— you can make reservations here. They offer live entertainment nightly, artisanal cocktails and craft beers aplenty all within the best atmosphere.
This was a great place to come to on the first night— calm, beautiful, excellent food and sorta low key, but in a good way.
Day 2— We woke up pretty early, and got ready for a full day of activities. First things first pick up the rental car from Cheap Rent a Car. This was $99 per day and not only one of the only options we could find with availability, but not a bad price. The rental car market in Hawaii is HOT so be sure to make reservations early to ensure you have a car.
From there we were off— we did our drive thru Covid Test at Walgreens and set out to our first destination. We had planned out a small loop near Oahu but fair warning, it takes about 30-45 minutes to get anywhere due to the traffic!
Hoʻomaluhia Botanical Garden was our first stop and it was so beautiful. You can drive or stroll through these incredible lush gardens with mountains in the back ground! There is an iconic picture spot on the road you drive in on, unfortunately you are not allowed to stop or get out of your car at this time. There is a guard at the beginning of the road and police regularly drive thru. We did get incredible shots in other places though! Admission is FREE and the gardens are open daily from 9am-4pm.
Up next we drove to Byodo-In Temple near by! This is another incredible destination with a lot of history. It was established on June 7, 1968, to commemorate the 100 year anniversary of the first Japanese immigrants to Hawaii. The Byodo-In Temple in O'ahu is a smaller-scale replica of the over 950-year-old Byodo-in Temple, a United Nations World Heritage Site in Uji, Japan. It costs $5 to enter here and is open 8:30am-5pm daily. You can buy tickets at the door.
After an amazing first two stops we grabbed our first acai bowl of the trip at Lanikai Juice— it was everything I was dreaming of and more!
We had a quick outfit change in Target and set out to hike the iconic Pill Box Hike! This hike is a moderate hike due to the steep elevation gain but the views are so incredibly worth it! I use Alltrails to scope out trails before I leave as you can often find recent trail conditions listed. You can find that here. It is a 1.8 mile trail, but 649 feet in elevation gain! We went in the late afternoon and it was perfect timing!
The trail overlooks Lanikai Beach— one of the best rated beaches in the world. You will need to park on the street and walk up to the tail head. There were plenty of signs. This trail features “pillboxes” that were originally used by the military. You can climb on top of them and even go inside if you’re brave!
We then walked down to hangout on Lanikai Beach for a little bit. There is public access all along the residental road and we brought towels to lounge on. You do not want to miss this crystal clear beach that draws people in for activities such as paddle boarding, kayaking, swimming and more!
If you’re feeling up for it you can grab a drink at the Edge of Waikiki before dinner. This is located back downtown at the Sheraton Waikiki with an infinity pool overlooking the beach.
For dinner we kept it casual since we had a jammed packed day. We got Marukame Udon Waikiki— these are the famed Udon Noodles and there is always a line around the corner for this place. You can order online and pick up to avoid the line. Highly recommend checking them out while you are in town— they are made to order and authentic! You can see their instagram here.
Day 3— We started our morning with Sunrise Shack for açaí bowls. OMG these are incredible. I had the Blue Dream Bowl and it was so so good. You will find this inside the Outrigger Waikiki Beach Resort. They also have an authentic ‘shack’ on the North Shore, but unfortunately we didn’t have time to make it out there.
Next up we set out to hike Makapu’u Light House Trail. We originally were going to hike Diamond Head Crater but they are closed on Wednesdays! So never the less, we found an incredible trail. The trail at Makapu’u Lighthouse is paved which is a plus! But the main attraction here is the tide pools you can hike down to. Technically they are closed but most people on the trail go down.
To see the tidepools you will hike almost until the end of the trail, where you will see a sign on the right side of the trail with a warning sign. This is where you start to descend down the mountain. There are white paint markers on the rocks to help guide you down. Once down there it is incredible sights! Waves crashing on the rocks— one thing you can do to be safe is check the tide reports. We were told by other hikers it was generally safe there until 10/11am that day. This changes often and you can check the tide reports here.
The hike is 2.5 miles, and paved unless you go down to the tide pools. There is a parking lot at the trail head, but it often fills up early with overflow parking on the street. You can snorkel in the pools and beware there are sea urchins so you need shoes to wear in the water!
Next up we stopped in Halona Blowhole Lookout— you can go down here and lounge on the beach and even swim in the water, but it looks a bit rough. We just stopped in to see the lookout.
We were dreaming of snorkeling in Hanauma Bay. You will need a reservation to enter here, which we didn’t know so we were unable to go. To ensure you can go here is what you need to know— they are closed on Mondays and Tuesdays. You will need a reservation which can be made here. The entrance fee is $25 per person and parking is $3 for visitors. Hawaii residents, active military or children 12 and under can enter for free.
We finished the afternoon on the famed Waikiki Beach and even got a sweet treat at Lappert’s Hawaii for an afternoon scoop of ice cream! So good! There is free public parking for Waikiki Beach you can navigate here with maps.
We couldn’t leave without going to a traditional luau! We decided on Chief’s Luau as they had incredible reviews. I will say, it was a bit cheesy, but I am glad we went. They offer 2 packages, we went with the cheaper— the Paradise Experience which included unlimited food, 2 drinks, and a lei upon arrival for $155. Personally, I don’t see a need to do the more expensive one. The show is great offering dances from all Polynesian Islands and history. It ends with fire dancing. In addition they offer round trip transportation to Waikiki for $40 which is a plus. It is located about an hour outside of the downtown area.
Our Covid Test finally came back while we were at the luau and we were cleared to go to Kauai in the morning!!! We got home and pack out bags!
KAUA’I
Day 4— We started our morning early heading to the airport for a flight to Kauai. We flew Southwest Airlines— they offer inter-island fight hoppers from $39 with free checked bags! You cannot beat these prices! You can search their flights here.
A short 30 minute flight and we were in Kauai! We went through the Hawaii Safe Travels screening again and picked up our rental car. This time we went with Turo— it is an app similar to Airbnb for cars. We had such an incredible experience, they brought the car to the airport for us complete with a welcome basket with tradition Kauai goodies and a lei!
Our first stop was to Java Kai for coffee and some food! It was incredible. I had the quinoa power bowl— all the food is so fresh and healthy tasting. I am always torn, because I want to try it all!
Right around the corner from Java Kai is Kauai Juice Co — super cute and worth popping in! In this area you will find very cute shops, restaurants and coffee shops! Worth looking around!
Next we headed out to Queens Bath— a unique tide pool formed by a sinkhole surrounded by igneous rock. There is a small hike down to this and parking is located within a residential area so you may have to wait until a spot becomes available because street parking is not allowed.
You can read more about the trail here, it is more like a short walking path in my opinion. It can be muddy and slippery so be cautious! In the winter the waves can be violent and it is often closed— do not go around a closed gate. People have been killed here! In the summer, when we were there, it was relatively calm and many people were swimming.
On the way back towards Poipu we stopped in Long’s Drug Store— a partner of CVS offering free Covid Testing. This will ensure we will have results within 72 hours to make it to Maui.
We arrived at the Sheraton Kauai Resort and it was beautiful! This resort is beachfront in one of the best areas to stay on Kauai. I was blown away, this hotel was recently remodeled and the rooms are excellent. They offer a pool over looking the breathtaking beach area with beach chairs and cabanas available.
For dinner we went to Merriman's Fish House. It was INCREDIBLE. Merriman’s offers a locally sourced, fresh, authentic cuisine. I highly suggest the Ono Fish Tacos. They were the best fish tacos I think I had the whole time in Hawaii. We watched the sunset while over looking lush palm trees and the ocean in the distance. You can make a reservation here.
Day 5— Today we have big plans so we grabbed a coffee and quick bite to eat at Dark Horse Coffee. Excellent service, they open at 7am daily. You should try the avocado toast!
Our big adventure of the day was zip lining with Koloa Zip Lining. We had an excellent experience. The tour offers 8 ropes over the course of 4 hours. You can even go upside down! Zipping through the jungle was so fun! There is a stop for local Hawiian juices or water too! Be sure to wear bug spray, or be prepared to fight some mosquitos out there.
For lunch you we grabbed a poke bowl from Koloa Fish Market and OMGGGG. This was recommended by our guides while zip lining. I was hesitant at first, because I don’t like raw tuna but they offer cooked shrimp and endless veggie options. There was a line around the building and for good reason. This was the best poke bowl I have ever had. The veggies tasted so fresh and had incredible flavor. I wanted to go back for seconds.
We headed back to relax at the resort. We spent some time at the pool, swam in the ocean and watched the surfers!
For dinner we went to the Beach House Restaurant. This place offers INCREDIBLE sunset views with panorama viewing as they are bring the outside in with sliding pocket doors. Be sure to make a reservation here before sunset so you can enjoy while you’re dining! Be sure to try the lobster deviled eggs for an appetizer!
Day 6— We had to start our day with an acai bowl per usual. This time we went to Little Fish Coffee— they serve acai bowls, bagels, coffee and more! I tried an acai bowl and a bagel sandwich. They offer picnic tables in the grassy area in front of their shop. There was a line here every morning so if you need to go somewhere in a hurry be mindful of this!
We went back to the resort to spend more time at the pool and beach! We even snorkeled here.
We really liked the bar here— Lava’s on Poipu Beach they served the best drinks and authentic Hawaiian cuisine!
Early this afternoon we set out for a Na Pali Coast Sunset Dinner Cruise with Blue Dolphin Charters. This was incredible! If you book online you can save $10— you can book here. We saw soo many dolphins and even saw a sea turtle. The coast in massive and taking it in from the water is magical.
You board the boat in the early afternoon to sail to the Na Pali Coast in time for sunset. They offer unlimited drinks, an excellent dinner and alcohol drinks on the way back to the dock. If you go on a cruise you will want to bring—
Sunscreen
Light Jacket or Windbreaker
Photo ID (For 21+ Access to Open Bar)
Motion sickness preventatives if necessary
Camera
Our Covid Test once again came back around 8pm and we were cleared for Maui!!!!
MAUI
Day 7— We headed out for the airport early this morning for our flight to Maui. We flew with Southwest Airlines again. This flight was not direct— we had a layover in Oahu. There were no direct flights from Kauai to Maui. Once we got into Maui we had to go through the Hawaii Safe Travels again— this was the longest line we waited in while on any of the islands. It took 30-40 minutes.
Once cleared, we picked up our rental car from Hertz— this was the only traditional rental car we used while on the islands and it was INSANELY expensive. But definitely necessary in Maui.
Once we packed our tiny car full of our luggage we got in and headed to our LAST Covid Test at Long’s Drug Store again! Thankfully this drive thru testing is super quick— takes about 5 minutes and most importantly FREE.
We headed for the hotel next— about a 45 minute drive from the airport.
We stayed in Kaanapali at Kaanapali Beach Hotel— they recently renovated their rooms and they are very nice. The area is perfect— right beside Whaler’s Village and Black Rock Beach, an iconic snorkeling spot. You cannot go wrong in Kaanapali.
For lunch we went to Maui Fish Market— so good. I had no idea I would ever be so into fish markets for lunch but yall! They are so good. On the way home we stopped in a gas station and bought snorkels to go check out the beach in front of our hotel— Black Rock Beach.
We got in our bathing suits on and our gas station snorkels and headed out to Black Rock Beach— the sea life was way more than I could have expected!!! So many fish and other animals, we even saw a sea turtle eating on the rocks! You can cliff jump here too. A GREAT place to snorkel— this is located right in front of the Sheraton Maui Resort and Spa.
We watched the sunset and had dinner at Hula Grill in Whaler’s Village. You can dine with your toes in the sand at this adorable beach side eatery! Make a reservation here.
Other dinner options in Whaler’s Village— you will need a reservation for any of these!
Monkeypod— HIGHLY recommended but we were unable to get in here. They also have locations in Wailea and Oahu. You can make reservations here.
Leilani’s on the Beach— offering incredible ocean front views with award winning dining! You can make a reservation here.
We finished the night with gelato from Ono’s Gelato! Such a great way to end the night.
Day 8— We got a later start than I would have liked, but we set out for the Road to Hana around 8am. While this does not sound late, we were staying on the west coast of Maui, so it was about a 45 minute drive to Paia, where the road typically starts.
You can read my very detailed blog post here. It includes all the best stops and what you can skip!
If you are doing the Road to Hana I HIGHLY suggest downloading the Gypsy Guides— Road to Hana, Maui, for $6.99 you will have an automated auto guided tour via an app. IMO this is a requirement as there is no cell phone service on the drive. It provides 140 audio points and alerts you when to stop. The app is guided by location and does not need cell phone service to work!
Day 9— Our morning started early as we were headed out with Pride of Maui on the Molokini Snorkeling Tour. Molokini is widely considered to be a world-class snorkeling destination—because of its unique crescent shape, it is protected from high winds offering calm waters and vibrant underwater life.
They served breakfast upon arrival and we were off to Molokini. At the first stop we snorkeled and snuba’d— which is a combination of snorkel and scuba diving. This was my first time to do it. You breathe through an oxygen regulator but you do not have to carry the tank on your back. The oxygen tank floats on the surface. It was an excellent experience and our guide was phenomenal!!
Once back on the boat we were served lunch and moved to Turtle Town— this is where you will see sea turtles. We were fortunate enough to see several!
On the way back we got cookies and they offered an open bar! Overall I would highly recommend this tour. The staff was so professional and ensured everyone’s safety and made sure a good time was had!
Since we were close to Paia we went back into town— we grabbed an acai bowl from Paia Bowls. They are sooo good! We continued to stroll the town. They have a lot of cute surf shops and little local places!
We went to Hookapu Beach— this is a famed place to see see turtles lounging on the beach. Today there was only about 3 but they were so cute!! You can also watch the surfers here too!
On our way back through town we got Hawaiian ice at Ululani’s Hawaiian Shaved Ice— this is a staple! You can find it on a few islands but we stumbled upon the location in Paia. Highly recommend. I had the POG flavor and it was the best shaved ice I have ever had!
To end the day we went into Lahaina— a town on the west coast but south of Kaanapali. They have a ton of shops, restaurants and treat stores to pop into off Front Street. We had sushi at Lahaina Sushi Ko— oddly enough we had been looking for sushi this whole trip and never really found any until here.
We also saw the Banyan Tree— a tree that takes up almost 2 acres! It was planted in 1873 after it was brought from India.
Other restaurants recommended in Lahaina:
Star Noodle— the famed noodle restaurant serving fresh, house made noodles!
Dirty Monkey— Bar and grill over looking the Front Street, offers live music.
Breakwall Shave Ice Co— home of the adult shaved ice, acai bowls, coffee and more!
HAWAII ISLAND (BIG ISLAND)
Day 10— this morning we got to eat at Island Vintage Coffee— a coffee shop that had been recommended by a local. It was fabulous! We had the best acai bowls and iced coffee!
On the way to the airport we stopped at Olowalu Juice Stand— it is the perfect photo op. The best part is it is located right beside a Maui Gold Pineapple stand. So we picked out pineapples to take home too! They can even package them up in a box to take as a carry on.
Another great stop right here is Leoda’s Kitchen and Pie Shop— serving the best fresh baked pies daily, they also serve breakfast, lunch and dinner.
Now on to our last inter-island flight with Southwest Airlines. This was another $39 steal and a very short hop over to the Big Island. The Safe Travel screening was the quickest and most nonchalant of any island! They maybe took 2 minutes and we were on our way!
We rented another car with Turo since we had such a great experience in Kauai! The car was waiting in the airport parking lot for us.
We hit the road to Da Poke Shack— yall this place was legit. There was a line out the door in the late afternoon and they were mostly sold out but we still had some options left. I recommend going early and prepare to stand in line.
We headed back to check into our hotel— Courtyard by Marriott King Kamehameha’s Kona Beach Hotel. This hotel was also recently renovated and not far from the airport. It was a great pick!
For dinner we went to Kona Brewing Co— there was a long wait but it was worth it. They offer many fresh made brews on tap and great pizza! While at dinner we devised a plan for tomorrow.
Day 11— we got a decently early start because we had planned a lot for today. We called it the “Road to Kona” because we planned to make a big lap around the island so we could see everything.
Our first stop was at Menehune Coffee Company — we got bagel sandwiches and an iced coffee and were ready to go!
Next we drove through what seemed like endless fields to Kalae— the southern most point of the United States. It is often thought this point is in the Florida Keys, but it is in fact located in Hawaii. There is even a cliff you can jump off here which is not encouraged. Personally I was way to scared to even think about jumping off. It is pretty high!
It is believed that the first Polynesians to arrive in the Hawaiian Islands disembarked here at Kalae somewhere between 400 and 800 A.D.
Right down the road, roughly 10 minutes you will find Papakōlea— aka the Green Sand Beach was the next stop on our tour! I have never heard of a green sand beach but there are four in the world! One of them is located right here on the Big Island. To get back here you will need a jeep or truck with 4 wheel drive or you must hike several miles in— roughly 2.5-3 miles one way. Alternatively you can pay $20 per person to get a ride in the back of a pick up truck driven by a local.
Personally this is what we did for times sake, but after seeing just HOW far back the beach is, I would do it again in a heart beat.
The green sand is so mystifying! I would highly recommend adding this to your stops on the Big Island. It sparkles in the light. The green is formed by a common mineral in Big Island lava called olivine, which stays deposited on this beach because it is heavier than the other components of the lava.
You can swim in the ocean here, but the current can be treacherous. We got in to about our waist as it was so hot! There are no facilities or life guards on duty so if you choose to get in the water please be observant and do so at your own risk,
Next up was Punaluʻu Beach— also known as the black sand beach is an incredibly beautiful black sand beach where you may also find sea turtles sun bathing or in the water when snorkeling. The beach is lined with beautiful palm trees that make for a great place to relax. Definitely add this to your list! You can bring a towel and hangout— no reservation required for this black sand beach!
We were starving because we had not had anything to eat all day, we found Lava Rock Cafe near the entrance of Volcanoes National Park. I got a chicken wrap and I was so hungry I ate every bite!
We entered Hawaii Volcanoes National Park and stopped by the ranger station so we would know where to go. They suggested going to the end of Crater Rim Drive to see the Kilauea Overlook. Then we stopped at the steam vents. It was so cool to see the steam coming out of the vents. This striking phenomenon is created as ground water seeps down to rocks heated by magma deep underground. The rocks are so hot that it vaporizes the water, returning it to the surface as steam— it is quite the site to see.
Thurston Lava Tubes were the highlight of the National Park for me! I had never been into a lava tube which is essentially a cave made from lava flow. To get here there is a short walk through a rain forest. It was incredible.
Be sure to bring your America the Beautiful National Park pass for entry— if not it is $30 per vehicle. You can purchase an annual national park pass here. They are $80 and well worth the money in my opinion!
Be sure to bring a jacket or sweatshirt to Volcanoes NP as it is COLD here! No one warned me and I was in a tank top freezing.
If you have extra time stop at Punalu'u Bake Shop in Naalehu town to try the famous Hawaiian sweet bread and malasadas! We were told about this by a local! They are open daily from 8:30-5pm.
On the way home we booked it to Shaka Tacoz— this came highly recommended by the locals! Great stop for dinner.
Last but not least we scoped out some gelato at Gypsea Gelato oh my gosh— the banana was soo good!!!
Day 12— we got up early for our last day in Hawaii. We are staying near the hotel/airport since we are leaving. First things first—Kona Coffee and Tea for some iced coffee. We also got some coffee beans to take back home. They have a farm and grow the beans right here on the Big Island! If I had more time I would love to visit the farm.
Next up a last morning acai bowl from Basik Acai Cafe — so good!!!! I wish I could bring them home with me to eat everyday. We strolled the streets as they have many shops in this area. One in particular that I loved was Tasty Kona boutique on Ali'i Drive featuring items from around Hawaii and select small businesses around the globe! Be sure to check them out!
For lunch we ate at Island Lava Java— of course I had Ono Fish Tacos one more time! They were so yummy!
Our last stop on the way to airport— some Hawaiian shaved ice from our favorite Ululanis!
To return to the mainland no Covid testing is required. You do have to clear an agriculture screening twice before boarding the plane to ensure you are not taking anything off the islands that isn’t allowed. We had a smooth trip home!
